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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Middletown vacation homes

A covered porch with two grey upholstered chairs and a small table, wooden railings, and a window with a curtain.

1. Tangerine Cottage spacious home

Tangerine Cottage spacious home
Middletown
The price is ￥23,747
￥46,544 total
includes taxes & fees
Oct 27 - Oct 28
Tangerine Cottage spacious home
A large, two-story house with a front porch, surrounded by a well-maintained lawn and a fence.

2. 15-Acre Gated Wine Country Estate and 7BR Mansion, Pool, Spa ,Sleeps 18

15-Acre Gated Wine Country Estate and 7BR Mansion, Pool, Spa ,Sleeps 18
Middletown
The price is ￥211,977
￥363,807 total
includes taxes & fees
Nov 1 - Nov 2
15-Acre Gated Wine Country Estate and 7BR Mansion, Pool, Spa ,Sleeps 18
A covered outdoor deck with a table and chairs, a grill, and a bottle of wine.

3. Cobb Mountain Chalet King Size Suite

Cobb Mountain Chalet King Size Suite
Cobb
9.2 out of 10, Wonderful, (30 reviews)
"My husband and I cannot stop talking about this beautiful, serene gem. Each room was immaculate. The sofas were so cozy and plenty of soft blankets! The market is equipped with everything & just a few minutes away. We are house hunting & can’t wait to return to the chalet!"
United States
Roberta F.
The price is ￥10,971
￥27,755 total
includes taxes & fees
Oct 14 - Oct 15
Cobb Mountain Chalet King Size Suite
A hallway with wooden walls and a blue door, leading to a room with a bed and a table.

4. Cobb Mountain Chalet Main Floor

Cobb Mountain Chalet Main Floor
Cobb
9.4 out of 10, Exceptional, (21 reviews)
"Beautiful view from the deck! Wind was blowing the tree in the evening and it was so peaceful. House had everything you could need."
United States
tabatha p.
The price is ￥13,820
￥33,897 total
includes taxes & fees
Oct 18 - Oct 19
Cobb Mountain Chalet Main Floor
A wooden deck leading to a building with a large window overlooking a lake and hills.

5. Bungalow on the lake

Bungalow on the lake
Clearlake
7.8 out of 10, Good, (8 reviews)
"Great little cottage for a good price. "
United States
Danielle C.
The price is ￥21,087
￥31,217 total
includes taxes & fees
Oct 13 - Oct 14
Bungalow on the lake
A wooden pathway leading to a house with a view of a lake and mountains.

6. Watefront Getaway w/ Mtn Views & Dock in Clearlake

Watefront Getaway w/ Mtn Views & Dock in Clearlake
Clearlake
8.0 out of 10, Very good, (4 reviews)
"We had a wonderful one-night stay at this waterfront home. The location is unbeatable: right on the lake with mountain views and a private dock, and it made a perfect home base for a show at Cache Creek Winery. The host was excellent, quick to respond with clear check-in instructions, and the place was spotless when we arrived. Comfortable beds, everything we needed for the weekend, and easy to find. We would happily stay here again and recommend it to anyone visiting Clear Lake."
United States
Alison
The price is ￥20,580
￥42,177 total
includes taxes & fees
Oct 13 - Oct 14
Watefront Getaway w/ Mtn Views & Dock in Clearlake
A bedroom with a large bed, a dining table with chairs, a small table with a lamp, and a view of the sea through large windows.

7. Entire Lake Front home on Beautiful Clearlake with Private Dock! See Pics!

Entire Lake Front home on Beautiful Clearlake with Private Dock! See Pics!
Lower Lake
9.4 out of 10, Exceptional, (6 reviews)
"Spent a quiet long weekend here with my family. Made use of the dock and fished nearly the whole time. This place was perfect for us. "
United States
Chris C.
The price is ￥39,182
￥79,868 total
includes taxes & fees
Oct 15 - Oct 16
Entire Lake Front home on Beautiful Clearlake with Private Dock! See Pics!
A modern kitchen with stainless steel appliances, grey cabinets, and a marble backsplash.

8. The Parlour House at the Fainting Couch

The Parlour House at the Fainting Couch
Cobb
The price is ￥68,271
￥84,829 total
includes taxes & fees
Oct 13 - Oct 14
The Parlour House at the Fainting Couch
A balcony with wicker furniture and a glass table, overlooking a scenic landscape during sunset.

9. Vineyard View Retreat • Fire Pit • Wine Tasting Perks

Vineyard View Retreat • Fire Pit • Wine Tasting Perks
Healdsburg
9.8 out of 10, Exceptional, (17 reviews)
"Great location!"
United States
Riley F.
Vineyard View Retreat • Fire Pit • Wine Tasting Perks
A swimming pool with a slide, a barbecue area, and a wooden deck.

10. 2 Hidden Wine Country Gem Upstairs Unit

2 Hidden Wine Country Gem Upstairs Unit
Scenic Brush Creek
9.8 out of 10, Exceptional, (31 reviews)
"We enjoyed our stay and would certainly use this rental again if we're ever in the area. "
United States
Glen M.
The price is ￥19,805
￥44,471 total
includes taxes & fees
Oct 15 - Oct 16
2 Hidden Wine Country Gem Upstairs Unit
A waterfront property with multiple buildings, a dock, and a palm tree.

11. Lakefront, 1 King Bed, dock, mist view, electronic firepit

Lakefront, 1 King Bed, dock, mist view, electronic firepit
Lower Lake
7.4 out of 10, Good, (3 reviews)
"Host was very welcoming and we had many amenities, including the dock, movies, and foosball. Overall, enjoyed the stay very much. Minor issues existed but were resolved fairly quickly"
United States
Vishnu N.
The price is ￥58,986
￥117,268 total
includes taxes & fees
Oct 15 - Oct 16
Lakefront, 1 King Bed, dock, mist view, electronic firepit
A spacious living area with a large window, wooden ceiling beams, and a cozy seating arrangement.

12. ❤The Elegant: A Chic Healdsburg Winery Cottage! Hot Tub, Views! !❤

❤The Elegant: A Chic Healdsburg Winery Cottage! Hot Tub, Views! !❤
Healdsburg
10.0 out of 10, Exceptional, (15 reviews)
"Awesome stay. Highly recommended"
United States
sharon p.
❤The Elegant: A Chic Healdsburg Winery Cottage! Hot Tub, Views! !❤
A living room with a red sofa, a green armchair, and a red armchair with patterned cushions. There is a coffee table with books and a lamp. The room has wooden flooring and a large window with blinds.

13. Napa Valley Retreat in Calistoga!

Napa Valley Retreat in Calistoga!
Calistoga
9.8 out of 10, Exceptional, (35 reviews)
"We had a wonderful day. Thanks for the flexibility on check-in day."
United States
linda k.
The price is ￥61,583
￥79,211 total
includes taxes & fees
Nov 1 - Nov 2
Napa Valley Retreat in Calistoga!
A wooden deck with outdoor furniture, a pool, and a view of a marina and hills.

14. Waterfront Luxury- 3 Plus Bedrooms

Waterfront Luxury- 3 Plus Bedrooms
Clearlake Oaks
9.4 out of 10, Exceptional, (29 reviews)
"2nd Flr Bedroom no TV / Out cactus cut visitor when passing by after backing in to the drive way / Roach in masterbed bathroom / Vaccumcleaner when used smelled like something died inside / there is a large wasp right side of the house we had to buy wasp deterrent for the weekend We loved the family room/ the outside patio and lights and the kitchen"
United States
Deanine W.
The price is ￥21,530
￥53,388 total
includes taxes & fees
Oct 13 - Oct 14
Waterfront Luxury- 3 Plus Bedrooms
An outdoor patio with a wooden deck, a table with chairs, and a door with a hanging light fixture.

15. Wine Country Farmhouse with Hot Tub

Wine Country Farmhouse with Hot Tub
Santa Rosa
10.0 out of 10, Exceptional, (75 reviews)
"The property was beautiful and the beds were so comfy! The property manager was very friendly and responsive. "
United States
Abigail M.
The price is ￥37,994
￥77,540 total
includes taxes & fees
Oct 14 - Oct 15
Wine Country Farmhouse with Hot Tub
A view of a lake with trees in the foreground and hills in the background.

16. Cozy Cottage: Panoramic Lake Views, WiFi, Deck

Cozy Cottage: Panoramic Lake Views, WiFi, Deck
Clearlake Oaks
8.4 out of 10, Very good, (14 reviews)
"Great communication from the property owner! Easy stay, well-appointed for our brief stay - beautiful lake views, sunsets, and sunrise!"
United States
Melanie B.
The price is ￥21,372
￥37,836 total
includes taxes & fees
Oct 13 - Oct 14
Cozy Cottage: Panoramic Lake Views, WiFi, Deck
A wooden deck with a metal railing overlooking a body of water, a stone sculpture, and a small pavilion.

17. STUNNING Lakefront, Huge DOCK,2 Kayaks, Sleep 8, Prime fishing spot

STUNNING Lakefront, Huge DOCK,2 Kayaks, Sleep 8, Prime fishing spot
Clearlake Oaks
9.6 out of 10, Exceptional, (61 reviews)
"This was the second time my family has stayed on this property and we enjoyed it very much. You’re right on the lake, so it’s very enjoyable for children to be able to fish and enjoy the water."
United States
Lauren R.
The price is ￥28,353
￥74,972 total
includes taxes & fees
Oct 15 - Oct 16
STUNNING Lakefront, Huge DOCK,2 Kayaks, Sleep 8, Prime fishing spot
A modern building entrance with a stone facade, a wooden pergola, and two wall-mounted lights.

18. Luxury Private Estate at Zoella Vineyards in the heart of Wine Country

Luxury Private Estate at Zoella Vineyards in the heart of Wine Country
Healdsburg
9.6 out of 10, Exceptional, (67 reviews)
"Unbelievable property – we will absolutely stay here again –Just fabulous!"
United States
Jeffrey S.
The price is ￥201,893
￥324,748 total
includes taxes & fees
Oct 17 - Oct 18
Luxury Private Estate at Zoella Vineyards in the heart of Wine Country
Private kitchen

19. Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape

Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape
Northwest Santa Rosa
9.4 out of 10, Exceptional, (23 reviews)
"very nice space "
United States
kevin c.
The price is ￥16,464
￥56,051 total
includes taxes & fees
Oct 13 - Oct 14
Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape
A kitchen with a stove, pots, pans, and a digital clock displaying 5:41.

20. Hilltop Hideaway: 4 acres, Hot Tub, Stunning Views

Hilltop Hideaway: 4 acres, Hot Tub, Stunning Views
Clearlake Oaks
The price is ￥23,509
￥57,956 total
includes taxes & fees
Oct 14 - Oct 15
Hilltop Hideaway: 4 acres, Hot Tub, Stunning Views
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Middletown Hotel Reviews

La Quinta Inn & Suites Santa Rosa Sonoma

La Quinta Inn & Suites Santa Rosa Sonoma

10/10 Excellent
"Easy access, central location, plenty of parking. Clean room, felt relativity new, no complaints for the the space."
Deanna 2-night trip
Posted 5 hours ago
La Quinta Inn & Suites Santa Rosa Sonoma

Find out more about Middletown

Middletown Vacation Homes information

Number of reviews
369
Accommodation
592 Vacation Homes
Lowest Price
￥27,755
Highest Price
￥363,807